27894-74-2

Upstream product

• 29019-41-8 p-Tolyl O-(2,3,4,6,-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 106-45-6 para-thiocresol 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 34213-32-6 lactose octaacetate 

Downstream Products

• 172949-32-5 p-Tolyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 1157902-59-4 C₃₆H₄₂O₁₅S 

Relevant academic research and scientific papers

MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates

Erbium(III) trifluoromethane sulfonate is proposed as a very gentle Lewis acid catalyst in a MW-assisted chemoselective method for the cleavage of isopropylidene acetals in awkward substrates by using pure water as the solvent.

Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates

In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio- and stereoselective couplings with partially protected pyranoside and furanoside acceptors. The methanesulfonate donors are prepared in situ from glycosyl hemiacetals, and are coupled under mild, operationally simple conditions (amine base, organoboron catalyst, room temperature). The borinic acid catalyst not only influences site-selectivity via activation of 1,2- or 1,3-diol motifs, but also has a pronounced effect on the stereochemical outcome: 1,2-trans-linked disaccharides are obtained selectively in the absence of neighboring group participation. Reaction progress kinetic analysis was used to obtain insight into the mechanism of glycosylation, both in the presence of catalyst and in its absence, while rates of interconversion of methanesulfonate anomers were determined by NMR exchange spectroscopy (EXSY). Together, the results suggest that although the uncatalyzed and catalyzed reactions give rise to opposite stereochemical outcomes, both proceed by associative mechanisms.

Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

Among five different oxidometallic species and two Lewis acids investigated, MoO2Cl2 shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations.

Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis

This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.

Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH 2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.

Programmable one-pot oligosaccharide synthesis

In an effort to develop a broadly applicable approach to the facile one- pot synthesis of oligosaccharides, the reactivity of a number of p- methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has b

SYNTHESIS OF TETRASACCHARIDE REPEATING UNIT OF THE K-ANTIGEN FROM KLEBSIELLA TYPE-16

Starting from L-fucose, D-glucose and lactose, methyl O--(1->4)-2,3-di-O-benzoyl-α-L-fucopyranoside and methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-α